A convenient and rapid method for the selective oxygen-17 enrichment of aspartyl peptides during solid-phase synthesis

Vassiliki Theodorou-Kassioumis; Nikolaos Biris; Constantinos Sakarellos; Vassilios Tsikaris

doi:10.1016/S0040-4039(01)01632-X

A convenient and rapid method for the selective oxygen-17 enrichment of aspartyl peptides during solid-phase synthesis

Vassiliki Theodorou-Kassioumis, Nikolaos Biris, Constantinos Sakarellos, Vassilios Tsikaris

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

Abstract

In this work we describe, for the first time, a rapid and efficient method for ¹⁷O selective labeling on the β-carboxyl group of an aspartic acid residue already incorporated into a peptide sequence anchored on a solid-phase support. The β-O-benzyl ester of the Asp residue of the Ac-RGD-benzydrylamine resin was successfully saponified using Na¹⁷OH in a methanol/dichloromethane mixture. The ¹⁷O selective enriched peptide was then released from the solid support by acidic cleavage. The ¹⁷O NMR spectrum confirmed the ¹⁷O labeling of the Asp β-carboxylate.

Original language	English (US)
Pages (from-to)	7703-7705
Number of pages	3
Journal	Tetrahedron Letters
Volume	42
Issue number	43
DOIs	https://doi.org/10.1016/S0040-4039(01)01632-X
State	Published - Oct 22 2001
Externally published	Yes

Keywords

Aspartic acid
Isotopic enrichment
O NMR
Oxygen-17
RGD peptides
Solid-phase O peptide enrichment

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(01)01632-X

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title = "A convenient and rapid method for the selective oxygen-17 enrichment of aspartyl peptides during solid-phase synthesis",

abstract = "In this work we describe, for the first time, a rapid and efficient method for 17O selective labeling on the β-carboxyl group of an aspartic acid residue already incorporated into a peptide sequence anchored on a solid-phase support. The β-O-benzyl ester of the Asp residue of the Ac-RGD-benzydrylamine resin was successfully saponified using Na17OH in a methanol/dichloromethane mixture. The 17O selective enriched peptide was then released from the solid support by acidic cleavage. The 17O NMR spectrum confirmed the 17O labeling of the Asp β-carboxylate.",

keywords = "Aspartic acid, Isotopic enrichment, O NMR, Oxygen-17, RGD peptides, Solid-phase O peptide enrichment",

author = "Vassiliki Theodorou-Kassioumis and Nikolaos Biris and Constantinos Sakarellos and Vassilios Tsikaris",

year = "2001",

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T1 - A convenient and rapid method for the selective oxygen-17 enrichment of aspartyl peptides during solid-phase synthesis

AU - Theodorou-Kassioumis, Vassiliki

AU - Biris, Nikolaos

AU - Sakarellos, Constantinos

AU - Tsikaris, Vassilios

PY - 2001/10/22

Y1 - 2001/10/22

N2 - In this work we describe, for the first time, a rapid and efficient method for 17O selective labeling on the β-carboxyl group of an aspartic acid residue already incorporated into a peptide sequence anchored on a solid-phase support. The β-O-benzyl ester of the Asp residue of the Ac-RGD-benzydrylamine resin was successfully saponified using Na17OH in a methanol/dichloromethane mixture. The 17O selective enriched peptide was then released from the solid support by acidic cleavage. The 17O NMR spectrum confirmed the 17O labeling of the Asp β-carboxylate.

AB - In this work we describe, for the first time, a rapid and efficient method for 17O selective labeling on the β-carboxyl group of an aspartic acid residue already incorporated into a peptide sequence anchored on a solid-phase support. The β-O-benzyl ester of the Asp residue of the Ac-RGD-benzydrylamine resin was successfully saponified using Na17OH in a methanol/dichloromethane mixture. The 17O selective enriched peptide was then released from the solid support by acidic cleavage. The 17O NMR spectrum confirmed the 17O labeling of the Asp β-carboxylate.

KW - Aspartic acid

KW - Isotopic enrichment

KW - O NMR

KW - Oxygen-17

KW - RGD peptides

KW - Solid-phase O peptide enrichment

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U2 - 10.1016/S0040-4039(01)01632-X

DO - 10.1016/S0040-4039(01)01632-X

M3 - Article

AN - SCOPUS:0035935176

SN - 0040-4039

VL - 42

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EP - 7705

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 43

ER -

A convenient and rapid method for the selective oxygen-17 enrichment of aspartyl peptides during solid-phase synthesis

Abstract

Keywords

ASJC Scopus subject areas

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